Case Study: Exiting a Family Business While Preserving Legacy

By the Greater Green Bay Community Foundation team

May 5, 2026 — As an attorney, CPA, or financial advisor, you likely work with clients who own closely held or family businesses. You may also recognize that philanthropy can play a strategic role in succession planning, particularly when a sale to a third party is on the horizon. But what does that look like in practice?

The following case study reflects a common scenario you might encounter.

When Mark and Elaine come in to update their estate and financial plans, retirement is only part of the discussion. At 66 and 64, they are financially secure, but after more than 30 years of ownership, they are beginning to plan for the eventual sale of their family business.

The conversation starts in familiar territory: income projections, portfolio sustainability, and options for gradually stepping away from daily operations. Depending on your role, you might model potential liquidity outcomes, evaluate tax exposure, review ownership structures, or assess contingency and transition plans.

The numbers are solid. A sale would easily support Mark and Elaine for the rest of their lives.

But as the discussion unfolds, a more nuanced issue emerges—succession beyond the balance sheet.

“Our adult children aren’t involved in the business,” Mark explains. “A third-party sale is the obvious path. We’re comfortable financially, but it’s still hard.” The business carries the family name and has long been tied to the couple’s identity and standing in the community. “If we sell,” he asks, “what happens to that?”

Elaine voices a different concern. “I worry about what happens within our family after the sale,” she says. “For years, the business has been what brought everyone together. I’ve seen families drift apart once that common purpose disappears.”

This is where you expand the planning conversation.

You acknowledge that a business sale is more than a financial transaction—it is also a personal and public transition. The way a family prepares for and navigates that change can affect both family dynamics and community relationships for years to come.

You introduce the idea of structured philanthropy as part of the pre‑sale planning process. Specifically, Mark and Elaine could consider contributing a portion of their closely held shares to a donor‑advised fund at the Greater Green Bay Community Foundation before any sale process is legally underway. When the business is later sold, the proceeds attributable to those shares would flow into the fund.

The tax mechanics are straightforward and compelling. A gift of closely held stock before a binding sale allows for a charitable deduction based on fair market value (subject to AGI limits), and any subsequent appreciation passes to the donor‑advised fund without capital gains tax.

But you are clear that tax efficiency is not the primary objective.

Establishing a philanthropic structure before a sale gives the family time—while the business is still operating—to define shared values, priorities, and a charitable mission. It sends a signal of continuity: although ownership may change, the family’s commitment to the community remains.

You suggest bringing the community foundation team into a future meeting. While you continue to manage the technical aspects of the transaction, the foundation’s philanthropic advisors can facilitate a different kind of conversation—one focused on issues such as:

• Which causes reflect the values that shaped the business
• How (and whether) the family name will be represented after the sale
• What governance role the next generation will play

You explain that the community foundation can also support structured family meetings, provide insight into local needs, and introduce best practices for multi‑generational philanthropy. This gives Mark and Elaine’s children a meaningful role before liquidity occurs. Rather than waiting for proceeds, they work together to evaluate opportunities, recommend grants, and represent the family in the community.

In many ways, philanthropy becomes a low‑risk forum for shared decision‑making and leadership development—without the pressures of running a business.

Mark and Elaine are receptive. Framing the plan this way makes the future sale feel less final and more transitional.

While every family business is different, this case illustrates how intentional philanthropy—designed in coordination with professional advisors and a community foundation—can help families exit a business while preserving values, relationships, and community impact.

We welcome the opportunity to partner with you as you advise clients through these transitions and would be glad to support the philanthropic planning needs of the families you serve.

Please note: the information provided is not intended to be tax advice. Donors should consult their tax advisors for personalized guidance.